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Synthesis of [2H5]arecoline for use as internal standard in mass spectrometric assay

✍ Scribed by H. Umesha Shetty; Timothy T. Soncrant; Nigel H. Greig; Stanley I. Rapoport

Book ID
102373818
Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
331 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Five deuterium atoms, three in the N‐methyl group and one each in positions 2 and 6, were incorporated into the cholinergic agonist, arecoline (1), methyl 1‐methyl‐1,2,5,6‐tetrahydropyridine‐3‐carboxylate, with 96% efficiency. Trideuterated pyridinium iodide (2) was reduced with sodium borodeuteride or sodium cyanoborodeuteride in acidic medium to yield [^2^H~5~]arecoline (3). Significantly greater deuterium incorporation occurred when 2 was reduced with sodium cyanoborodeuteride. This reduction process is discussed. The synthesized labelled compound was determined to be a suitable internal standard for mass spectrometric assays.

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